Ethanol → Ethyl 2-(4-fluorophenyl)-3-(4-methyl-4H-1,2,4-triazol-3-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968076노트

반응식

HRID 1968076 반응식
[F:1][C:2]1[CH:19]=[CH:18][C:5](/[CH:6]=[N:7]/[C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][O:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[CH3:20][N:21]1[CH:25]=[N:24][N:23]=[C:22]1[CH:26]=O.[O-:28][CH2:29][CH3:30].[Na+].C(O)C>C(OCC)(=O)CC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]2[CH:26]([C:22]3[N:21]([CH3:20])[CH:25]=[N:24][N:23]=3)[C:29](=[O:28])[C:30]3[C:13]([C:12]([O:11][CH2:10][CH3:9])=[O:17])=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7]2)=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 157078954-methyl-4H-1,2,4-triazole-3-carbaldehydeHCID 178519076HCID 178519076, 화합물

생성물 1

HCID 67259937Ethyl 2-(4-fluorophenyl)-3-(4-methyl-4H-1,2,4-triazol-3-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate수율 11%

시약·촉매·용매 1

HCID 7749Ethyl Propionate용매

반응 조건

온도
0 °C

실험 절차

A mixture of compound (E)-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one (690 mg, 2.7 mmol) and 4-methyl-4H-1,2,4-triazole-3-carbaldehyde (300 mg, 2.7 mmol) in ethyl propionate (20 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol [sodium (250 mg, 10.8 mmol) in ethanol (10 mL)] was added dropwise. After the addition the mixture was stirred at room temperature for 2.5 hr, then was quenched with water (20 mL) and solvent was removed in vacuum. The residue was dissolved in water and extracted with ethyl acetate three times, washed with water and brine, and then evaporated to give the crude product, which was purified by chromatography to obtain a yellow solid (120 mg, yield 11%). LC-MS (ESI) m/z: 395 (M+1)+.

후처리

  1. additionAfter the addition the mixture
  2. customwas quenched with water (20 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate three times
  6. washwashed with water and brine
  7. customevaporated
  8. customto give the crude product, which
  9. customwas purified by chromatography

출처 및 근거

ORD 기록
ord-ccc24085e0384696af699a91c0f0a01b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420650B2

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